Abstract
AbstractDedicated to Professor Emeritus Miha Tišler on the occasion of his 75th birthdayTreatment of methyl (S)‐5‐[(E)‐(dimethylamino)methylidene]‐2‐oxotetrahydrofuran‐5‐carboxylate (2) with potassium cyanide in acetic acid gave (S)‐5‐[(E)‐cyanomethylidene]‐2‐oxotetrahydrofuran‐5‐car‐boxylate (3), which was used as chiral dipolarophile in 1,3‐dipolar cycloadditions. Reactions of 3 with diazomethane (4) and nitrile oxides 5a‐c afforded spirolactones 6–8 in 24‐34% diastereomeric excess, while with diazomethane (4) in the presence of triethylamine, methyl 3‐cyanomethyl‐2‐methoxyfuran‐5‐carboxylate (12) was obtained.
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